Triethylamine → HCID 69731788, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-aminomethyl-phenyl)-pent-4-enoic acid methyl ester (1.67 g, 6.55 mmol) in dichloromethane (50 cm3) at ambient temperature under an atmosphere of dry nitrogen was added triethylamine (4.56 cm3, 32.8 mmol) followed by dropwise addition of methanesulfonyl chloride (1.52 cm3, 19.7 mmol) over 5 minutes. The mixture was stirred for 4 hours at ambient temperature and the filtrate volatile fractions removed in vacuo to afford a crude yellow oil. The oil was dissolved in ethyl acetate (100 cm3), washed with saturated sodium bicarbonate (2×50 cm3), brine (25 cm3), dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to a crude yellow oil. The oil was purified by column chromatography (silica, eluting with hexane-ethyl acetate 4:1 to 1:1) to afford the title compound as a pale yellow viscous oil (1.85 g, 100%) with a positive ion ESI (M+H)+296.2.

Provenance & Evidence